title: Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B.
abstract: The preparation of Kyn-containing peptides is difficult, owing to the low reactivity of Kyn in the coupling reaction. In this report, Kyn-containing peptides were efficiently obtained via on-resin ozonolysis of the corresponding Trp-containing peptide. In addition, a Kyn-containing cyclic peptide, cyclomontanin B, has been synthesized by this strategy in the combination with serine/threonine ligation (STL)-mediated cyclization.
authors.affiliation: Department of Chemistry, The University of Hong Kong, Hong Kong, P. R. China. xuechenl@hku.hk.
authors.forename: Clarence T T
authors.initials: CT
authors.lastname: Wong
authors.forename: Hiu Yung
authors.initials: HY
authors.lastname: Lam
authors.forename: Xuechen
authors.initials: X
authors.lastname: Li
mesh_terms: D003500:Cyclization; D007737:Kynurenine / Q000737:chemistry*; D008968:Molecular Conformation; D010126:Ozone / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D010455:Peptides; D010456:Peptides, Cyclic; D012117:Resins, Synthetic; C000588454:cyclomontanin B; D007737:Kynurenine; D010126:Ozone; D014364:Tryptophan